diff --git a/transport/ssh/ssh.go b/transport/ssh/ssh.go
index 0275fc1..e030a82 100644
--- a/transport/ssh/ssh.go
+++ b/transport/ssh/ssh.go
@@ -19,9 +19,10 @@ type Transport struct {
 	sess  *ssh.Session
 	stdin io.WriteCloser
 
-	// indicate that we "own" the client and should close it with the session
-	// when the transport is closed.
-	ownedClient bool
+	// set to true if the transport is managing the underlying ssh connection
+	// and should close it when the transport is closed.  This is is set to true
+	// when used with `Dial`.
+	managed bool
 
 	*framer
 }
@@ -40,10 +41,36 @@ func Dial(ctx context.Context, network, addr string, config *ssh.ClientConfig) (
 	if err != nil {
 		return nil, err
 	}
+
+	// Setup a go routine to monitor the context and close the connection.  This
+	// is needed as the underlying ssh library doesn't support contexts so this
+	// approximates a context based cancelation/timeout for the ssh handshake.
+	//
+	// An alternative would be timeout based with conn.SetDeadline(), but then we
+	// would manage two timeouts.  One for tcp connection and one for ssh
+	// handshake and wouldn't support any other event based cancelation.
+	done := make(chan struct{})
+	go func() {
+		select {
+		case <-ctx.Done():
+			// context is canceled so close the underlying connection.  Will
+			// will catch ctx.Err() later.
+			conn.Close()
+		case <-done:
+		}
+	}()
+
 	sshConn, chans, reqs, err := ssh.NewClientConn(conn, addr, config)
 	if err != nil {
+		// if there is a context timeout return that error instead of the actual
+		// error from ssh.NewClientConn.
+		if ctx.Err() != nil {
+			return nil, ctx.Err()
+		}
 		return nil, err
 	}
+	close(done) // make sure we cleanup the context monitor routine
+
 	client := ssh.NewClient(sshConn, chans, reqs)
 	return newTransport(client, true)
 }
@@ -56,7 +83,7 @@ func NewTransport(client *ssh.Client) (*Transport, error) {
 	return newTransport(client, false)
 }
 
-func newTransport(client *ssh.Client, owned bool) (*Transport, error) {
+func newTransport(client *ssh.Client, managed bool) (*Transport, error) {
 	sess, err := client.NewSession()
 	if err != nil {
 		return nil, fmt.Errorf("failed to create ssh session: %w", err)
@@ -78,10 +105,10 @@ func newTransport(client *ssh.Client, owned bool) (*Transport, error) {
 	}
 
 	return &Transport{
-		c:           client,
-		ownedClient: owned,
-		sess:        sess,
-		stdin:       w,
+		c:       client,
+		managed: managed,
+		sess:    sess,
+		stdin:   w,
 
 		framer: transport.NewFramer(r, w),
 	}, nil
@@ -104,7 +131,7 @@ func (t *Transport) Close() error {
 		retErr = fmt.Errorf("failed to close ssh channel: %w", err)
 	}
 
-	if t.ownedClient {
+	if t.managed {
 		if err := t.c.Close(); err != nil {
 			return fmt.Errorf("failed to close ssh connnection: %w", t.c.Close())
 		}